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There is value to this comment. My thinking is more like.. Here is a car in the trailhead parking lot... It only takes 2 minutes to boost a car, less than that to break in. IMO the windshield note is no more incentive than the simple presence of the car in the lot. But then of course I drive cars that nobody in their right mind would want to steal.

I understand it's controversial about which school to subscribe. I prefer to use my "trailhead car" which is old and ugly enough to deter most thoughts of valuables being inside. That being said, while someone can break in in a couple of minutes, knowing that it will not be reported for a day or so can make it more enticing than an unknown arrival.

Where in KY do you live? If near the Red River Gorge (hereafter referred to as RRG) There are plenty of short hikes with easy bail out points (Or backtrack) if you get into trouble.
KY has a lot of nice areas to hike in, or if close to the Ohio River, it's a short drive into Ohio or Indiana for similar experiences. And of course if in S KY, there is always the Smokies in TN.

BTW: I have hiked solo since I started hiking, so: No, it's not a stupid idea!

When you have a backpack on, no matter where you are, you’re home.
PAIN is INEVITABLE. MISERY is OPTIONAL.

I find I really like my solo trips. They have a different quality than trips with others. I'm a bit more cautious when traveling solo, more conscious and more deliberate where safety is concerned, since there is no "help" available if something were to go wrong.

"The more I carry the happier I am in camp; the less I carry the happier I am getting there" - Sgt. Rock

Also test your gear in similar conditions (back yard?) just so you're not miserable if it isn't up to the task. Play with your gear so you know it well.

Decide what you "Need to bring" then go over that gear and get rid of half of it cause you're likely at 50lbs already Go over it again and find the stuff you missed (oops!! Forgot food and water!)

Get out there and have fun!!!

Yea, what XexorZ says.

Most of us have been there, "I really NEED that 8 Lb Axe" or something similar. And, for some trips an axe is needed (Trail maintenance, Extreme winter camping) but you will find when you get home, even after you "get rid of half of it cause you're likely at 50lbs already" you will find you did not use, or likely did not even think to use, half of what is left. I carried binoculars for about 9 years in the early days, I thought to use them ONE TIME, I did not actually use them, just thought "Hey, I got Binocs, I could use them here!" Then headed up the trail. I don't carry them anymore.

ALSO, as "X" says, practice in a stable location before going out.

I see (read too fast first time) you are planning a RRG trip already, Be aware that cell phone's sometimes work, & sometimes don't in the gorge. PM me for some suggestions for a first hike, well, actually one. I think you will like it, a lot!

When you have a backpack on, no matter where you are, you’re home.
PAIN is INEVITABLE. MISERY is OPTIONAL.

One option to consider is to contact your local Boy Scouts. Teaching backpacking skills is their business and they are always looking for adult leadership. Make sure and pick a troop that is "into" the backpacking and outdoor experiences you are looking for.

Learn new skills, meet people who want to (and do) backpack, and give back to the community. Great win-win.